"I Went Undercover on America's Cheating Website"

We wish we could ignore ashleymadison.com, the online playing field for married people looking to cheat. But over 8 million men and women have signed up, heeding its slogan, "Life is short. Have an affair." Eight. Million. REDBOOK couldn't ignore that number, so we sent writer Lisa Taddeo online to meet up with straying husbands and get them to answer: Why?Related: Women cheat online, too. Our male reporter met up with one of them.

Most Read

By definition, Ashley Madison, a dating site for cheaters, is a disreputable place. Seedy, sad. Your first impulse may be to throw your arms up in rage and condemn its members, the ones trawling for an affair or the chance to talk dirty in an instant message. But don't you also have questions? I set out to ask married men on the site not only why they cheat, but why they do it so boldly, admitting their recklessness and confessing their betrayals on the Internet as though their morality and fidelity were items up for auction on eBay.

To get started, I create a profile with a fake name and a dark picture of myself and chart a plan. I'll respond only to men who approach me. Then I'll meet a few of them for a drink, but there will be no drunkenness. For my own safety, I won't reveal what I'm really doing. And if they try anything, I'm gone.

In my profile, I say that I'm married, because in addition to avoiding escorts, many of the men on the site don't want the complications of seeing a single woman. They want an even trade. Your fidelity for mine. The rest of what I say is mostly true, and to weed out the more aggressive guys, my tone comes off as exploratory, not sexual. I write about being curious. I say I miss autonomy. I say I'm scared to live the rest of my life with unexplored desire.

Overnight I receive 164 messages.

Several of them contain below-the-waist images. One of the men has a tagline on his profile that reads, "At your cervix, madam." Within moments of signing in, instant messages flush my screen, emails and winks from muscular men and men much older than me and young ones and proud fathers and one gray grandfather, worming out like monsters from the baseboards. Do you want to chat? Hey beautiful. Hey sexy. Alone in my house, and naked for you. And then, a familiar face. A man I know. He wants to meet; he doesn't know I ran into him just last week. Maybe I shouldn't be surprised: 68 percent of the site's members are men, and their average age is 44 — right in his demographic. But my jaw hits the ground anyway when I realize whom I'm looking at. He's married with children. A family man. Or so I thought.

The more careful among them don't post pictures directly to the site, but they send a key that grants me access to a "private showcase" of images. Some wax their chests and others are darkly forested. One man takes a picture in front of his 1987 Camaro, parked outside of a diner. One man has his arm across the shoulders of a young Jon Bon Jovi. But most have taken their pictures recently and surreptitiously. In their bathrooms with their iPhones held up to the mirror, their faces partially obscured, their wives' J'adore behind them, on top of the toilet.

There are the ones who just want to meet to have sex; you can tell because their handles are direct and uncomplicated: Yours4Lust and DeepPassionMan. They list measurements and ask for yours, as though it's merely a matter of fitting one puzzle piece into another. I ignore these. Instead, I respond to the thoughtful ones, whose tales might help answer my questions.

SEX ONLY SCRATCHES THE SURFACE

In between his kid's soccer game and a pizza party, B.* sends a picture of himself on a golf course. Earlier, he sent 2,000 words on how he got into the game, the trips to California and Ireland, the way the clouds flood the greens at Galway Bay. He also included a dispatch from the previous evening's softball game, from the excitement of the opening huddle to the crushing defeat.

We are getting to know each other. It is moving quickly. The long puppyish emails, the condensation of an entire life into a few breathless paragraphs that allow him to retell the stories his wife has already heard. He lets himself be vulnerable too, sharing memories of the beloved dog he had to put down, the long drive home from the vet when he could not stop crying.

We have not spoken on the phone, but that's normal when you meet online. It doesn't matter, because he says he can imagine my voice; he says he knows exactly what it must sound like. When he is standing on the soccer field and children are moving around in a blur, he says, he slips out of the game and thinks of me, and if his BlackBerry vibrates in his pocket, he hopes that it is me.

He tells me he had a brief affair with a woman from one of his company's offices. He joined Ashley Madison because that encounter left him wanting more. Not sex, necessarily. "Everything about her consumed my thoughts, and that's when I first signed up. It was partly out of curiosity, but also largely my attempt to take my mind off her." He was attracted to my fears about losing my independence. He says they mirror his own.

You think this is a site for sex in motels, private and dirty with condom wrappers in the folds of the sheets. Ashley Madison's president, Noel Biderman, certainly does. He says that the men are there for one thing. "They're saying, 'I want a type of intimacy my partner's not giving me,'" he says. "This is about sex."

It's true that one of the first men I meet fits that profile perfectly. F. tells me he can't have the kind of sex he wants to have with his wife because she's unwilling, and, on some level, he doesn't want to do those sorts of things with her. He complains that she performs oral sex as if it were a chore. He says he likes it rough, and tells me he cheated for the first time a few months ago. He was in Vegas for a bachelor party, and he took a girl from the blackjack table upstairs to his room. It was wild, he says, and then puts his hand on my leg. F. is 32, tall and slim, and has been married for two years. He's been with his wife since they were just out of college. They recently had a child. I remove his hand from my leg; I tell him he doesn't look like a father. He says he doesn't feel like one. He says he did not marry the wrong woman, that he'd want to stray no matter who he was with. That's why he doesn't feel guilty. "This is human nature," he says, and he winks. I say I have to go.

Biderman is right about types like F., but wrong that all the men on Ashley Madison want sex and sex alone. There are plenty of men like B., who says he is happily married when what he really means is he is complacently bored. In one of his emails, he says he can't write too much, but there are 800 words, and pictures of him and his children. They are beautiful, the son eating an ice cream cone, the young girl in overalls. B. is holding her up and she is grabbing his finger, and the finger is wearing a wedding ring. His message says, "Although we haven't yet met, something has happened (at least for me). I get a smile on my face when I have an email from you."

He wants something from me that is not sex, even if it is disguised as sex. Here on a site where the idea, ostensibly, is to facilitate no-strings-attached affairs, a lot of men are trying to forge real bonds. B. might be looking to fall in love.

"AM I MISSING OUT?"

H. is an engineer in his early 30s who practices birdcalling in his spare time, and sends me pictures of his younger days, when he went boating and life was dangerous and uncharted. "Why is it I get the feeling I'm missing out on something very important?" he asks in an email. "Will I ever not feel like I'm missing something?" He is intensely curious; he thinks a lot. His inner life is full. Maybe, he ventures, he's selfish. "Either way," he says, "it's driving me crazy."

What's terrible is that H. isn't even married yet. The woman he is thinking of cheating on is still only his fiancée. He says she's as close to perfect as any man could hope for, but it's clear he's conflicted. He believes that marriage is a path all men must travel at some point. If they've dated a woman for X number of years, marriage comes next, an obligatory stop on the endless conveyer belt. The union is doomed before it begins.

H. wants to meet me, but he's not sure he can steal time away. For now, he is content to write — to paint the picture of the moment we lock eyes across a bar. He says checking his email is his favorite time of day. He thinks of me at work, he thinks of me when he is birdcalling. He thinks of me when he is having dinner with her.

On Ashley Madison, wives are mostly reduced to pronouns, and in that reduction they are less a human than a fact that shares their home. In the most extreme, these pronouns — to whom the men claim to be happily married — become antiheroes to the plan. "She just canceled her dinner, so now I can't meet you on Tuesday. Dammit, dammit, dammit."

All of the men tell me that their wives would never guess they are doing this. "There's no reason," says one suitor. "I've never been caught." This one has had affairs before. He has gone home to his wife after renting a room and having sex there with another woman.

B., who is kind and polite and describes himself as honest despite what he's doing at this very moment, says his wife isn't the nosy kind. "She would never check my BlackBerry. I know a lot of women who do, but my wife really trusts me."

Like the other men, he's afraid of getting caught but, similarly, says he feels no guilt. As such, this relationship — the one with me — is a village in a different country, on another planet.

"I COULD NEVER HAVE THIS CONVERSATION WITH HER"

I meet G. at a vodka bar. He calls me by my fake name, and I call him by his. (There are different honesties in an affair. You may get to know a deep tumor of the married man's soul, but you won't know his real name.) He looks exactly as he does in his pictures: dark-haired and big-chinned, vaguely politician-ish. Having sworn off alcohol, he orders a water.

G. is in his mid-30s and works in finance, though he wanted to be a scientist. He lives in a big city now but grew up in a small town where he married young. He no longer believes that monogamy is tenable. I am the second woman he has met from the site.

The screen on his phone is taken up by an image of his baby daughter; he moves it aside with his thumb and forefinger to search for a book I tell him he would like. G. has trouble with eye contact, so he says to his water, "You're beautiful."

He has never eaten caviar, so we order a flight. His wife is not intellectual enough, he says, but he will be with her for life. He didn't realize when he married her that a little under a decade later he would be bored. He knew he was smarter, but she was beautiful and kind, and that was enough for him then. We talk about books, and he says his wife doesn't excite this part of his brain. "I could never have this conversation with her," he says. "She would start talking about the baby, or moving out of the city." She does not wear lingerie for him, like she used to. He expresses whole hollows of neglect.

This man is somewhat detached, but also eager as a boy. A scientist poking at his marriage in a petri dish, outlining the shape of his discontent. He didn't have sex with the first woman he met from the site, so he doesn't feel guilty.

He says that in order for his home life to move forward, he needs outlets like this: caviar and water with a strange woman on a rainy Tuesday. He never makes a move on me, but he tries to set up the same time next week. As though he were a respectful single suitor, he is taking it slow.

TALKING ABOUT GLORY DAYS

Some of the men are more practiced. T. is a professor. He is well read and a little dirty ("I like illicit encounters. I like mystery and secrets, and I like some risk from which tremendously pleasurable rewards might be won. I like making out. I like burying my face between my partner's thighs…"), but mostly he is interested in the sound of his words on my screen.

The one thing all of these men relentlessly share is the desire to tattoo a swath of themselves onto a bare and willing canvas. I have not heard their best stories, like the time they scored the winning touchdown for their high school team. Their best selves are their past selves. They want to get lost in a Springsteen ballad, and I am the time-travel machine.

T. is also paranoid. "Perhaps you could tell me a little about your fantasies, or perhaps you could reassure me that you're not using me as a research subject for a book," he writes. I don't tell him he's right, but I don't tell him he's wrong, and still he wants to meet. He says he would love to get coffee next week, or "alternatively, we could simply meet at the park, and then take a room at the city's nicest pay-by-the-hour hotel — yes, I have been there, and no, it's not nearly as seedy as it sounds."

It is excitement grafted onto fear that makes T. want to meet me. Like the others, he never calls what he's doing cheating but, rather, "seeking pleasure outside of the relationship." He asks what my curfew is, as if we are teenagers testing boundaries.

Based on T.'s first name and a bit of information he has given me, I can easily figure out that he's a popular professor. (On a teacher-rating site, some of his female students discuss how sexy he is, the little heart of his smile.) He also publishes his darkly sexual poetry online, and I wonder if his wife has read it, and if so, if she's at all suspicious about the sort of man her husband is.

"I MISS THIS"

There is something haunting about these men. They are here because they no longer feel a certain strain of sexual excitement coursing through their veins, and Ashley Madison, in many ways, is a quick fix. Simply by signing up, they're back in the world of seeing a name in an inbox that makes your pulse thump. They relive the passing-notes part of early love, when futures seem flexible and bright and your life looks the way you imagined it, like you are the star of your own movie and not the production assistant on your family's documentary.

"It's amazing how much, even when you are fulfilled and happy, the spark of something like a secret kiss can illuminate just how narrow our experience is," says H., the engineer. "Have you heard the analogy that life is like a funnel? That you start off with such a wide range of possibilities, and as you tie yourself to things through the years (spouse, bills, house, kids, career), the range narrows until one day you're pretty much completely restricted at the tip of the funnel? Have you ever heard that?"

That night, G. from the vodka bar writes to me about the book recommendation. He loves it, he wants to discuss it; when can we see each other again? He says he has developed a taste for caviar. He wants some, after the long weekend.

When I meet K., a 28-year-old newlywed, at a dark brandy bar, it takes him a few moments to ask if I'm waiting for someone. I tell him I am, and slowly he takes the seat beside me. This is the type of bar where men know their drinks and the years of their scotch, but K. only mumbles to the bartender about Dewar's. Right away, he tells me that he's nervous, but that I don't scare him. He says the scary part is that he wants to do this.

He says that he and his young wife like to entertain their friends on the deck of their apartment on the weekends. They like to do all the things a new couple likes to do, though K. has very quickly replaced his we with an I.

"I love to cook and go to restaurants, watch a bunch of movies, sporting events — you know, all the normal stuff that when done repeatedly would make someone sign up for a site like this."

There is a simple revelation there. Young K. has nailed it. He actually thinks an affair will help his relationship. Like G., he thinks this will be a respite. A brief cold shower to cool the need he can no longer — after only a year of marriage — ignore.

He tells me that just a few weeks ago, he and his wife threw a party. She made martinis and he grilled porterhouses. "It was a blast," he says. They did not have sex afterward because they were tired, but they still have sex a few times a week.

"I love having our friends over, but when everyone goes home, it's just us again. She's really great, she's really pretty. I just miss not knowing how my night is gonna end." Gesturing toward me and the whole of the bar, the women looking for men and the men looking at women, he says, "I miss this."

ON TO THE NEXT

One of the most striking things about Ashley Madison users is that they can literally be anybody. Though they are all different, they are also all the same, a composite man.

This composite man likes scotch. He drinks it on the rocks, but only if he drinks at all, because he might also drink only water. He is a lawyer and a professor and a doctor and an engineer and a caller of birds, and he went to college but he didn't have enough fun. He plays golf and he works out but he has a belly he didn't have in college, when he was having more fun. This man has children and is married to a beautiful pronoun. She adores the kids and is an excellent partner. They have sex once a week, once a month. On his birthday she did what he wanted in bed, but he thinks she treated it like doing laundry.

I end communication with all of them by not replying to their emails. Having had no physical contact, having not even exchanged phone numbers, it's surprising that some of them assume a level of ownership over me and our "relationship." A few keep trying. They think there's a problem with the server, because they thought we had something. Some tell me they think my husband found out, and that's why I've dropped off.

Eventually they all disappear, which is why I'm surprised when several weeks later I receive an email from G., the financier who liked caviar. But then I realize it isn't intended for me.

"Hey Lindsay, really looking forward to dinner tonight."

Despite all the soul-baring emails and the "you're beautifuls," G. has moved on to another partially obscured photograph on Ashley Madison. Like most of these men, he just wants someone to listen, anyone to type back. Perhaps he'll meet her somewhere dark and lovely. Perhaps he'll tell her she is the second woman he's connected with from the site, or even the first. It doesn't much matter what he says. Nobody will ever be the only one.

*Some details have been changed throughout.

Outraged? Worried? After reading this story, you might want to check his browsing history or grab his phone. Normal? Sure. But don't do it, says Scott Haltzman, M.D., author of The Secrets of Happy Families. "Instead, use this article as a starting point to talk about your fears and ways to keep things fresh," he says. Haltzman's tip: Try something — anything — new together, regularly.

But don't be clueless, either, says Michele Weiner-Davis, M.S.W., author of Divorce Busting. "If he's changing screens when you walk in or staying up online after you go to bed, say something instead of snooping when he's gone," she says.